Page 8 of Accidentally Falling For My Best Friend (Chicago Awakenings #2)
PARKER
THIRTY YEARS OLD
May
Y ou would think that after twenty-one years as Oakley’s best friend, I’d be used to the whole “super wealthy” thing.
But there will always be that part of me that remembers how relieved Mom was to learn about the scholarships I qualified for at my school after Dad passed, or how stressed she was about paying bills while we were waiting for the money from Dad’s life insurance.
I was so afraid that I would not only lose my dad, but the first real home I’d ever had, the first school where I’d fit in. My first real friend.
Moving around so much, and then losing Dad so unexpectedly, taught me to never take anything for granted. I know how quickly things can change or be taken away. I try not to take any of the luxuries that I’ve been afforded in life for granted.
Oakley on the other hand, sometimes needs reminding that not everyone is used to his lifestyle.
“Don’t you think taking them on your yacht for a private sunset cruise on Lake Michigan might be a little over-the-top for a first date?
” I call out to him from where I’m finishing getting ready in my room.
“Won’t it seem like we’re trying too hard, or maybe even be creepy that we’re isolating them on the water like that? ” I worry aloud.
“Um, noooo,” Oak reassures me with a laugh, answering from his room next to mine.
“We’re not ‘isolating them’. They’ll have their best friend there, it is a double-date after all.
Plus, there’s a whole crew on the boat,” he reminds me.
“And they live in our building so I’m sure they’re also used to a certain level of luxury.
It’s not too much Park, it’s showing we cared enough to put in the effort to organize something nice,” he says, and I can hear the smile in his tone.
It’s early May, and the season to take out his boat has only just started.
I’m fairly confident that’s his main motivation for this date, not impressing them with his “efforts,” but I don’t bother to bring that up when I know how much he loves being on the water.
It’s always nice to see how happy he is when we’re out there.
“Wow, someone cleans up well,” Oak says with a whistle as he enters my room. I roll my eyes at his remark before noticing we’re in similar clothes.
“Should I change so we don’t look like we coordinated our outfits?
” I ask. We both have on dark designer jeans, with the sleeves of our button-ups rolled up to expose our forearms, and a sweater tied around our shoulders for when the wind picks up on the lake.
“We look like we’re auditioning for a sailing commercial,” I grumble.
“We look fantastic and the sweaters are practical,” he assures me with a smirk, obviously less concerned with what people will think of us matching. “Are you ready to meet the girls?” he asks.
“I guess so,” I agree, making sure that I have everything before we head down to the lobby.
We’re a few minutes earlier than the time we agreed to meet, but we thought it would be more polite to wait for them in the lobby than at their door in case they didn’t want us to know the exact unit they’re in yet.
Both girls are clearly excited as they exit the elevator and see us waiting, practically bouncing over to us. I like how cheerful they seem. I’ve noticed I prefer to surround myself with animated, peppy people, like Oakley, and they definitely seem to fit that description.
When it’s obvious to me that the people around me are happy and are having a good time, I’m less anxious about my own behavior and wondering if I’m fitting in.
I can just relax. But if I’m with other shy, introverted people, like myself, I tend to stay quiet because I’m so worried about what they're thinking or that I’ll say the wrong thing and make things even more awkward.
“We all match!” Aspen says brightly, giving my forearm a light squeeze as she laughs.
The girls have a similar boating look, with expensive looking button-up blouses and sweaters of their own, although they opted for skirts and will probably have cold legs if we’re outside on the water.
I’ll have to remember to offer her my sweater.
“I’m not sure which look I like more, you hot and sweaty in the gym, or all cleaned up here for a date,” Sage tells Oakley. He’s one of those guys who never has to put in any effort and still ends up looking like a model.
“Well, I can think of a few other looks I’d like to show you in my apartment,” he responds, with an overly flirty tone and a wink, earning more laughs from the girls.
I don’t know how he always manages to pull off the cheesy flirty thing, not that I really have any desire to, but even if I did, I could never be that confident. I’m sure it only works because of how attractive he is, but women eat it up.
“You look beautiful,” I say in a softer tone to Aspen as we all turn to exit the building, and her smile grows even bigger.
“Thanks! You always look really good, too” she adds with a slight drawl I hadn’t noticed during our brief first meeting. She must be from the South.
We make our way to Oakley’s driver, who’s waiting out front to take us to the pier.
Oakley’s family has a long list of people they can hire out to do odd jobs like staffing his yacht for a private date.
I don’t even want to think about how much tonight probably costs.
I know logically that I make a lot of money now, especially as the new CFO, but I’ll never have Caldwell money.
Once we arrive, the crew reminds us of the safety procedures before we’re escorted to a romantic dinner they’ve set up on the deck.
There’s a table formally set for four with red rose petals contrasting against the stark white of the tablecloth, and after pulling out a chair for Aspen, I end up across from her and next to Oakley.
His presence at my side relaxes me like it always does, and the conversation between the four of us is easy.
I’d forgotten how much I enjoyed going on double dates with Oak, how much more fun they are when he’s there to remind me I’m not being socially awkward and I don’t have to overthink everything.
The girls are obviously very close with each other as well. They constantly finish each other’s stories, and the admiration in their gazes when they look at the other is sweet.
“We didn’t meet until college, but we’ve been attached at the tit since we were roommates freshman year,” Sage explains with her own faint Southern accent. Oak bursts out laughing before I can even register her unique phrase, but she goes on like nothing happened.
“We both knew we wanted to spread our wings a little after college, though, so we moved away from our families and up to Chicago,” Aspen adds.
“My father wasn’t very excited about me moving so far away and ditching the life he had planned for me, but he makes sure that we video call a lot.
Plus, he takes the jet up here when he really wants to see me, and Sage’s parents do the same thing,” she adds.
I can tell her comment sets Oakley at ease, it’s obvious they come from extreme wealth like he does.
Oak’s always been very vocal about wanting his storybook happily ever after.
The wife and kids with the big mansion in the suburbs.
But, one of the many reasons that he’s struggled to find this elusive “perfect” wife, is that so many women are only after his family’s name and the lifestyle that they think is attached to it.
That’s part of why I was surprised that he went so all-out planning this first date, but I guess that he was right about them having money of their own if they can afford to live in our building.
I’m aware that the other reasons he’s still single have to do with me and our “codependent” friendship, so I try not to focus on them and the guilt that I feel about potentially holding him back.
I know it’s not my decision, and if he wants space from me to date more, I won’t stand in his way.
No matter how much I dread the fact that he’ll no longer be my roommate one day.
Maybe Aspen and Sage will be less likely than our exes to complain about us living together, how much time we spend together, or how often we bring the other up in conversation. They’re the same way with each other.
I don’t think there’s anything wrong with our friendship because I know how lucky I am to have Oak in my life, and I’ll never take it for granted.
Oakley has also assured me, and any of his exes who dared question our relationship , that anyone he ends up with will understand how important I am to him.
I’ll never feel like I deserve that level of loyalty from him, even if I love it.
Even after all of these years, there’s that small part of me that’s confused about what he sees in me, why he chose to be my friend when everyone else labeled me as awkward.
Sage and Aspen seem just as close as we are, though, so this could be the perfect set up.
The whole “wife and kids” future has always seemed a little less certain to me than it has to Oak.
Maybe it’s because of my grief over losing Dad like I did that I haven’t been able to picture myself with a family of my own one day, or maybe I just haven’t found my person.
I don’t hate the idea. It’s definitely easier to imagine that type of future for myself if Oakley and I had wives who were also best friends.
We could live next door to each other and raise our kids together.
That wouldn’t be too different than having him in the room next to mine.
And I know it would make him happy to have a big family like the one he grew up in and has always wanted.
Alright, slow down, this is a first date, not a marriage proposal. I don’t need to put that kind of pressure on tonight.